Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents

doi:10.6023/cjoc202304008

Abstract

Asymmetric dearomatization reactions can transform planar, achiral aromatic compounds into chiral compounds with three-dimensional structures, making them as an important strategy for the preparation of chiral molecules, drugs, and natural products. Chiral hypervalent iodine reagents are widely used in asymmetric oxidation due to their advantages of mild reaction conditions, environment friendliness and excellent enantioselectivity. The dearomatization reactions induced by chiral hypervalent iodine reagents in the past 20 years are summarized. According to the different chiral skeletons, they are divided into chiral lactate derivatives, binaphthyl, tartrate, spiro rings, heterocycles, and other skeletons such as carbohydrate, [2.2]-para-cyclophane, triptycenes, etc. Each type of these chiral reagents is introduced in detail from the aspect of preparation, asymmetric reactions, and typical examples. In addition, the application of dearomatization reactions induced by chiral hypervalent iodine reagents in the total synthesis of natural products is also summarized.

Key words: chiral hypervalent iodine, dearomatization, asymmetric synthesis, natural product

Cite this article

Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.

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Fig. & Tab. 30

Scheme 1. Synthesis of chiral iodine compound 5a

Scheme 2. Synthesis of chiral iodine compound 13

Scheme 3. Synthesis of chiral iodine compound 34

Scheme 4. Synthesis of chiral iodine compound 47

Scheme 5. Mechanisms for asymmetric dearomatization of naphthol 8a induced by chiral hypervalent iodine reagents

Scheme 6. Synthesis of chiral hypervalent iodine compound 65

Scheme7 Asymm. etric dearomatization/[4+2] cycloaddition of phenols 22 induced by chiral hypervalent iodine compound 65 Asymmetric dearomatization/[4+2] cycloaddition of phenols 22 induced by chiral hypervalent iodine compound 65

Scheme 8. Synthesis of chiral iodine compound 70

Scheme 9. Possible intermediates of dearomatization of 8a induced by chiral iodine compound 70

Scheme 10. Synthesis of chiral iodine compound 77

Scheme 11. Synthesis of chiral iodine compound 80

Scheme 12. Synthesis of chiral hypervalent iodine compounds 86

Scheme 13. Synthesis of chiral hypervalent iodine compound 92

Scheme 14. Mechanism of dearomatization of phenols mediated by chiral hypervalent iodine compound 96

Scheme 15. Synthesis of chiral iodine compound 105

Scheme 16. Synthesis of chiral hypervalent iodine compound 109

Scheme 17. Synthesis of chiral iodine compound 112

Scheme18. Mechanism of dearomatization of naphthols 8 mediated by chiral iodine compound 112

Scheme19. Mechanism of dearomatization of naphthol 8a mediated by chiral iodine compound 108

Scheme 20. Synthesis of chiral hypervalent iodine compound 125

Scheme 21. Synthesis of chiral iodine compound 129

Scheme 22. Synthesis of chiral iodine compound 132

Scheme 23. Synthesis of chiral iodine compounds 135 and 137

Scheme 24. Synthesis of chiral iodine compound 145

Scheme 25. Synthesis of chiral iodine compound 151a

Scheme 26. Synthesis of chiral iodine compound 157

Scheme 27. Synthesis of chiral hypervalent iodine compound 162

Scheme 28. Synthesis of chiral hypervalent iodine compound 167

Scheme 29. Synthesis of scyphostain analogues 173 and 176

Scheme 30. Total synthesis of (–)-maldoxin

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